the checklist trap

How To Avoid The Life As Endless Checklist Trap

“Growth for the sake of growth is the ideology of the cancer cell.”

– Robert Levine

Do you ever feel like time is slipping out of your control?

What about this one – working more efficiently is the only way to tackle all your to-do’s?

What if this endless quest to be more productive is just making things worse?

In “Why Time Management Is Ruining Our Lives”, Oliver Burkeman shines a spotlight on life for people like you and me in the early 21st century:

“What is uniquely modern about our fate is that we feel obliged to respond to the pressure of time by making ourselves as efficient as possible – even when doing so fails to bring the promised relief from stress.”

That’s a scary thought. If my productivity-boosting systems add to my stress instead of reducing it, why the hell am I doing them!

Cost Benefit Analysis

When I was in my late teens and early 20’s I spent a lot of time at the gym. My sophomore year of college all 3 of my roommates played football. I didn’t have an excuse except that I’d played sports all through high school and it made sense to keep up the daily routine. And, I liked the results.

Needless to say, my obsession was driven by vanity, not health or a sports scholarship…something that has taken 20+ years to reverse itself.

As I entered the working world it grew harder and harder to find the time (and energy) to work out. By my early 30’s, a pattern started to emerge: 

1) Start new exercise routine with full motivation 2) Slowly lose motivation and adjust routine 3) Phase out of routine

After about ten years of repeating the pattern I realized it was a zero-sum game. Depending on the fun factor, some routines lasted longer than others. But unless I could maintain the routine over the long haul, the little muscle mass or physical limberness would quickly fade.

Yes, I did something good for my mind and body, even if temporary.

BUT, I often ended up feeling more frustrated than when I began.

Think about that for a second. What started as a way to improve myself and break down stress, ended up causing me more.

So it is with Inbox Zero and other clever systems designed to help you be more productive or efficient with your time – the second you let up, the emails start piling up. Which in itself isn’t such a bad thing…unless the sight of a previously clear/now full inbox adds to your stress.

As Mr. Burkeman observes, “the truth is that more often than not, techniques designed to enhance one’s personal productivity seem to exacerbate the very anxieties they were meant to allay”.

SisyphusOr for the time-management chasers, “the better you get at managing time, the less of it you feel that you have”.

Don’t feel too bad. After all, the idea that managing your time and working more efficiently may one day help you get everything under control is damn attractive.

However, the stream of incoming emails is endless. And unless you can create a system that’s going to effectively respond to the emails and remember the important parts, Inbox Zero is great for Sisyphus but not the rest of us.

By the way, you’re never going to maintain that deep brown tan from your holiday so why even start with the solarium?

The Law of Diminishing Returns

What about goal setting and the clear benefits of setting personal and professional goals?

Yes, there are benefits such as increased focus and motivation, but some potential pitfalls, as well.

For example, too narrow a focus can cause you to overlook important aspects or developments of a task. Furthermore, if you relax once you achieve a goal, you could be limiting yourself if you had kept pushing for more.

The biggest pitfall I see is that goals can eliminate the power of randomness – a critical success factor for creativity and innovation.

As Anisha Vinjamuri of InnovationsIQ warns: “Innovation comes from a certain degree of chaos and randomness…extreme goal setting kills creativity”.

If you consider the modern workplace’s demand for agile projects and people, take note of Vinjamuri’s advice:

“As much as setting rigid goals gives us a sense of security, real growth comes from being able to handle and manage randomness. Much of it ties back to positive personality traits that are essential for growth in any profession like flexibility, adaptability, less resistance to change, and openness to new ideas.”

Don’t take her word for it. Think about your own biggest accomplishments – did you set goals to achieve them?

A lot of my professional success has come from right time. My side hustle as a voice actor, for example.

I could never have set a goal to do this type of work as I wasn’t even aware of the profession. Randomness in action.

Ancient wisdom teaches us that you’ll find what you’re looking for when you’re not looking for it.

There’s another aspect of productivity to think about: Self-improvement.

In “The Disease of More”, Mark Manson calls self-improvement for the sake of self-improvement a “glorified hobby”.

However, Mr. Manson rightly points out that the “improvement is not the problem, it’s the WHY that’s
motivating the improvement that matters (remember my exercise routine).

Staying with Greek mythology: “When one compulsively looks to improve oneself, without any greater cause or reason driving it other than self-aggrandizement, it leads to a life of immense self-preoccupation, a light and beneficent form of narcissism where one’s constant attention and focus is on oneself…ironically, this will probably make your life worse off”.

Something else that will make your life worse is the futile chase after a “better me”.

If this is what’s driving you, you are probably split in two pieces –  a “good you” who is going to improve the “bad you”.

How’s that working out for you?

The Unexamined Life Is Not Worth Living

Don’t get me wrong – I believe the desire to improve oneself is a natural and a valid one. I also believe that too many goals and priorities can lead to none.

Setting goals is a great way to stretch yourself and/or your team. It can also can provide a motivating common purpose to rally around.

But often, in life as in work, “Less Is More“. Life is not a checklist or a competition – with others or yourself.

If you find yourself traveling to new places to add to your “cool places” list or enhance your Instagram or Facebook profile rather than for the simple pleasure of going someplace new, I’d say you’ve got the wrong motive.

On the subject of time away from work, do you feel pressure to be productive in your leisure time? Or to show your Facebook friends how much fun you’re having on holiday?

Another characteristic of modern life is that even in rest and recreation we’re preoccupied with efficiency.

Where do you stand? Ask yourself: “Can I relax for relaxing sake…or am I just recharging my batteries so as to enable more work?”

Here’s an undeniable fact:

We all have our own processes. Our own systems that work or don’t work for us. With specific drivers based on the collection of our unique experience.

Despite what that super coach or self-help guru may tell you, no one can tell you how best to (or not to) spend or manage your time.

They can tell you what has worked for them. No more.

My best advice for navigating the slippery slope of self-improvement is to PAY ATTENTION TO WHAT’S DRIVING YOU.

Look at your patterns and pay attention to how you feel when your exercise routine falls away, your inbox fills up, etc.

To help you reflect on your unique situation, here’s a simple 3-step process:

  1. Reflect on your drivers:

Q: What’s motivating me to improve? To go faster? To save time?

  1. Reflect on your trade-offs:

Q: By improving in one area, what’s the trade-off (e.g. more time at fitness studio, less time reading)?

  1. Reflect on your processes/systems:

Q: Which of my systems is helping? Which ones need to be adapted or thrown out?


It’s important to understand your preferences – what you like, don’t like; what you want, don’t want.

For this reason, it’s good to have goals and be consistent in your decision-making process.

It’s just as important to be aware of the goal-setting pitfalls and keep in mind that when you get too strategic you risk losing the element of spontaneity and randomness.

Remember the wise words of TED superstar Brene Brown – “we are emotional beings who on occasion think”.

For my FREE ADVICE on how to avoid the endless checklist trap, drop me a note and let’s chat.

  • Tim, great piece of writing and refreshing. Self improvement is indeed a cult and a terribly puritanical and narcissistic one at that. In many ways, it is the new religion, with public displays of good deeds (look at my last marathon on facebook for instance … blah blah blah) and with it comes the implied public shame of those lesser mortals that don’t do boot camp, dont have a fabulous inner life, or are not validated in their career and all the trimmings ….

    Ive got no answers either.

    I do know that the alternative is bad for me too …. and maybe the cult works for many of us ??

    • Yes, it is a very efficient cult, for sure. Either way, lazy or diligent, most important is to be aware of what’s driving me. Thanks for sharing!

  • Perceptive article Tim. Great bit of insight there. How often do we see others (or, heaven forbid, recognize in ourselves) this tendency to fall in to counterproductive circular logic? Wasting time being stressed about not having time to become less stressed is a classic. Or being dogmatic in our decision making rather than intuitive and adaptive.
    Good stuff.

  • Hi Tim, I was cheering as I read this. Yes!! Leave space. Let things emerge. When I do this many of the things that emerge are in the direction of my goal, just in a more creative way. A way I wouldn’t have thought of beforehand.

    I’m starting to wonder if ‘busyness’ is a form of depression for people at work. It’s too hard to stop and face how I really feel, it’s easier to just stay busy, to just reach one more goal. It can be scary to stop and face yourself sometimes. I can feel a piece of writing from me coming on in response to your great piece. Thanks Tim for the thought provoking article.

    • Hi Maggie, thanks for sharing your thought! Glad the article provided some positive impulses for you. Yes, perhaps we can add depression to the distraction that busyness causes…question is, what came first?